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  • Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them.

Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them.

Bioorganic & medicinal chemistry (2009-03-03)
Hamid Sadeghian, Neda Attaran, Zeinab Jafari, Mohammad Reza Saberi, Seyed Mohammad Seyedi, Hossein Eshghi, Mehdi Pordel, Mohammad Mahdi Riazi
ABSTRACT

A group of 4-methoxyphenylacetic acid esters were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compounds 7d-e showed the best IC(50) in SLO inhibition (IC(50)=3.8 and 1.9 microM, respectively). All compounds were docked in SLO active site and showed that carbonyl group of compounds is oriented toward the Fe(III)-OH moiety in the active site of enzyme and fixed by hydrogen bonding with hydroxyl group. It is assumed that lipophilic interaction of ligand-enzyme would be in charge of inhibiting the enzyme activity. The selectivity of the synthetic esters in inhibiting of 15-HLOb was also compared with 15-HLOa by molecular modeling and multiple alignment techniques.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
4-Methoxyphenylacetone, ≥97%
Sigma-Aldrich
Eugenol, ≥98%, FCC, FG
Sigma-Aldrich
Methyl eugenol, ≥98%, FCC
Sigma-Aldrich
4-Allyl-1,2-dimethoxybenzene, 99%
Sigma-Aldrich
Eugenol, natural, ≥98%, FG
Sigma-Aldrich
4-Allylanisole, 98%
Sigma-Aldrich
Eugenol, ReagentPlus®, 99%
Sigma-Aldrich
4-Allylanisole, ≥98%, FCC
Supelco
Eugenol, PESTANAL®, analytical standard